LEXINGTON, Ky. – When Gary Contessa emailed his owners last May to round up investors to buy the colt now known as Rydilluc, he predicted that the dark bay son of Medaglia d'Oro would be their Kentucky Derby horse.

Contessa knows something about Derby horses. He's picked them out, bought them and trained them – and then sold them before they made it to Churchill Downs. Chief among them: Peace Rules, winner of the Louisiana Derby and Blue Grass before taking third in the 2013 Kentucky Derby as part of Bobby Frankel's barn.

Now Contessa, a mainstay on the New York circuit since 1985, believes he has his first Derby horse for keeps in Rydilluc. The colt is the co-second choice in Keeneland's $750,000 Toyota Blue Grass Stakes but very well could go off the favorite Saturday off his three impressive turf victories, capped by Gulfstream's Grade III Palm Beach at Saturday's 1 1/8-mile distance.

"I've always sold them," the father of five said of his prospects. "We put a lot of kids through college selling really top horses."

However, this time Contessa's longtime owner Len Green bought out those partners who wanted to take the money.

"This horse, when he broke his maiden, in Gary Contessa-style, was for sale -- $300,000 or $400,000," Contessa said of his $150,000 2-year-old purchase. "Everybody looked at him. Nobody produced. Then we won the allowance race, and it became a feeding frenzy…. I can't tell you how thankful I am that Leonard Green stepped up to the plate."

Contessa did come to the Derby as an assistant to Stanley Hough when the stable's Proud Appeal was 18th in 1981 and Reinvested third the next year. Since then, he's been rooting for his former horses.

"People say to Gary, 'How can you watch that horse go to the Derby and you sold it and you're not training it?'" Jennifer Contessa said of her husband shortly before Rydilluc blew out three-eighths of a mile in 37 2/5 seconds. "He's like, 'Everybody wins. How can I be upset?'

"(But) I've never seen Gary more excited about a horse. This horse is very special, and I see how positive Gary is and Eddie (assistant trainer Eddie Fernandez) is. Everybody feels it. He's very professional. It's like he goes to the track and says, 'I'm a winner.' And to be honest with you, it's Gary's time. He's been in this business a long time, and he deserves a shot."

Rydilluc (pronounced RYE-dill-LUKE) was named by partner Sean Shay for young family members named Ryan, Dillon and Luke.

Contessa said he's rarely been so confident as when Rydilluc ran for the first time. Then Rydilluc came into the Belmont paddock, looked around, got up on his hind legs and started hollering at the top of his lungs, as if he was a stallion entering a harem of mares. The last thing on his mind was running.

It's called losing the race in the paddock, and Rydilluc lost by 22 lengths.

Contessa and his staff have been prepared ever since, including extra manpower and 10-gallon buckets of ice water to get Rydilluc focused on the job at hand rather than his career down the road. He is schooled repeatedly in the paddock, including during the races at Keeneland.

"When you train a horse and they come to the paddock, let's call it stallion-esque, and they are ready to breed mares, you immediately starting to think, 'I can't believe I'm going to have to geld this horse,'" Contessa said. "That is a complete distraction for 99 percent of the horses. Generally it's a real negative.

"…Every start for this horse – even the Palm Beach – he comes into the paddock on his hind legs, screaming, carrying on, but doesn't sweat. First time out, he started out very cool, calm and collected and caught us off guard. The second, third and fourth starts, we were prepared for him. But once he goes to the track, he is all business."

Rydilluc, who is ridden by 2006 Derby winner Edgar Prado, probably has to finish first or second to get enough Derby points to make the May 4 race. If he does, the looming question will be if Rydilluc's dirt disaster was an unfair test or if his future indeed is on turf.

"But you just don't know how he's going to make the transition from grass. He's bred to, being by Medaglia d'Oro out of a Clever Trick mare. But nine times out of 10, horses who are exceptional grass horses aren't as effective on dirt."

The Derby victories by seeming turf horses Barbaro (2006), Big Brown (2008) and Animal Kingdom (2011) only contribute to Contessa's roses-colored glasses. He says Animal Kingdom, who won Turfway's Spiral before trying dirt for the first time in the Kentucky Derby, "set the bar for this move we're doing Saturday.